Most leadership teams have been planning for 2026. Budgets are taking shape, roadmaps are being discussed, and technology decisions are beginning to solidify. The risk at this stage is not a lack of planning. The risk is locking in assumptions that have not been fully validated.
Technology decisions made now will influence cost, risk, and operational flexibility well into the future. A concise review at year end can help leadership teams confirm they have addressed the fundamentals before plans are finalized.
The checklist below is designed as a leadership level pressure test. It highlights the areas that most often deserve a second look before heading into the new year.
Infrastructure and Core Systems
Infrastructure decisions often carry long term implications. Capacity assumptions, upgrade timelines, and architectural choices made during planning cycles tend to persist longer than intended.
Leadership teams should confirm:
- Core systems can support projected growth and operational changes through 2026
- Aging infrastructure or deferred upgrades are clearly documented and intentional
- Cloud, hybrid, and on-premise decisions are tied to business needs, not habit or convenience
The key question is not whether infrastructure works today, but whether it supports how the organization expects to operate in the coming years.
Cybersecurity and Risk Governance
Cybersecurity continues to evolve from a technical concern into a board level risk. Insurance requirements, regulatory expectations, and threat complexity are all increasing.
Before finalizing plans, leadership teams should confirm:
- Security policies are documented, current, and aligned with how the organization operates
- Incident response ownership and escalation paths are clearly defined
- Cyber insurance requirements and coverage assumptions are understood and realistic
Cybersecurity planning should be treated as a governance responsibility, not a collection of tools.
Identity, Access, and Permissions
Access tends to drift as organizations grow. Role changes, temporary exceptions, and contractor access often accumulate quietly over time.
Leadership teams should confirm:
- Regular access reviews are performed and enforced
- Privileged accounts are limited, monitored, and justified
- Access models reflect how people actually work today
Misaligned access is one of the most common and preventable sources of security and compliance risk.
Backup, Recovery, and Business Continuity
Most organizations believe they are protected because backups exist. Fewer have validated that recovery expectations match business reality.
Before heading into 2026, leadership teams should confirm:
- Backups are regularly tested and results are documented
- Recovery time expectations are understood and acceptable
- Business continuity assumptions align with current operations
Backup planning is not about technology. It is about resilience and confidence in the face of disruption.
Vendor, Licensing, and Cost Control
Technology costs rarely spike all at once. They grow gradually through renewals, license creep, and unmanaged vendor relationships.
Leadership teams should confirm:
- Auto renewals and contract timing are understood before they occur
- License usage aligns with actual needs
- Critical vendors have clear ownership and accountability
Intentional vendor management helps prevent cost surprises and complexity later.
Ownership and Strategic Oversight
This is where many organizations struggle most. Technology decisions are often fragmented across departments, vendors, and internal teams.
Leadership teams should confirm:
- There is clear ownership for technology planning and alignment
- Decisions are tied to business goals, not just operational needs
- Strategic oversight exists beyond day to day IT support
Without accountability, even well intentioned plans can drift.
A final Leadership Check
Most organizations are already planning for 2026. The most effective ones take time to pressure test their assumptions before those plans are locked in.
This checklist is not about adding new initiatives. It is about confirming that the fundamentals have been addressed and that leadership has clarity and confidence heading into the new year.
At TRC, we work with leadership teams as a Strategic Technology Partner and fractional CTO, helping organizations align technology decisions with long term goals. A short, focused review at year end can surface gaps, validate assumptions, and reduce uncertainty before 2026 begins.